Propose a plausible mechanism for the following transformation and justify the stereochemical outcome (J. Org. Chem. 1999, 64, 4617-4626): حمد CO₂Me Step 1 Incorrect. Heat MeOH co,Me Add any remaining curved arrow(s) to draw the first step of the mechanism. H₂C HC OCH Edit Drawing H₁C CH
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- Propose a plausible mechanism for the following transformation and justify the stereochemical outcome (J. Org. Chem. 1999, 64. 4617-4626): CO₂Me Heat MeOH MeO ° CO₂Me Step 1 Add any remaining curved arrow(s) to draw the first step of the mechanism. H₁₂C H.C ་་་་ H₂C O-CH3 Edit Drawing CH₂но CH3CO₂Et LDA, -78 °C NaOEt EtOH in addition to the mechanism predict which product is favoredQ12. (1bremeetblbenzene 1 ydergOesan elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance.
- Mustard gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagentlejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off le Island in Okinawa. (a) Label each double bond in iejimalide B as E or Z. (b) Label each tetrahedral stereogenic center as R or S. (c) How many stereoisomers are possible for iejimalide B? CH;0 CHO OCH, HO, iejimalide BWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH,nucleophilic substitution yields an optically inactive solution. When theisomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OHunder the same conditions, nucleophilic substitution forms an opticallyactive solution. Draw the products formed in each reaction, and explainwhy the difference in optical activity is observed.
- Draw a plausible mechanism for the following transformation H₂O* Z-I H3. Propose a plausible mechanism for the following transformation: & Q & CF3 H₂N CN 'N CF HOHWhich compound is the major product of the reaction sequence shown? (1) SOCE (A) (B) OH OH (2) (CH3);CO Na (CH3);COH (C) (D) O Na Na CI Compound D Compound A Compound C Compound B
- What effect would you expect the following changes to have on the rate of the Sy2 reaction of 1-iodo-2-methylbutane with cyanide ion? (a) The CN- concentration is halved, and the l-iodo-2-methylbutane con- centration is doubled. (b) Both the CN- and the 1-iodo-2-methylbutane concentrations are tripled.Draw a plausible mechanism for the reaction shown below. Provide explanations for each step in the mech- anism. CH3 H cat. TSOH R CH3 H3C NBn H;C N Bn(d) Determine the structure of the product or the reaction conditions in the following transformations; provide a curved arrow mechanism for each transformation: MnO₂ Acetone OH OH 1) O3, MeOH 2) Me₂S 1) LDA then PhSeBr 2) H₂O₂ ? Q: OH